Iodoethane → HCID 46208105, compound

Participants

Reaction Steps

A mixture of 3-(3,4-difluorophenyl)azetidin-3-ol (0.3 g, 1.62 mmol) triethylamine (0.68 ml, 4.87 mmol) and iodoethane (0.19 ml, 2.44 mmol) in tetrahydrofuran (15 ml) was stirred at ambient temperature for 15 h. The solvent was evaporated and aqueous hydrochloric acid (50 mL. 10%) was added and the mixture was washed with tert-butyl methyl ether (2×50 ml). The aqueous phase was made basic by addition of aqueous sodium hydroxide (5 M) and extracted with tert-butyl methyl ether (2×50 ml). The combined organic phase was dried (Na2SO4) and evaporated under reduced pressure to give the crude product (0.26 g). Purification by flash column chromatography on silica gel (ethyl acetate/methanol 1:1) gave 0.2 g (58%) of the title compound. The amine was converted to the fumaric acid salt and recrystallized from methanol/diethyl ether: M.p. 177-179° C. MS m/z (relative intensity, 70 eV) 213 (M+, 1), 141 (86), 127 (45), 114 (58), 58 (bp).

Provenance & Evidence